Originally Posted by Nothin but blue skies
I've done the Med cruise three times, one the first week of May and twice in October. October is nice but can be rainy, but May was almost perfect weather. I would avoid the summer months at all costs due to the heat and crowds in the ports and you also have a lot more children on the ships in the summer months.
Whatever you decide, try to fly in at least one day prior to the start of the cruise to rest and possibly see some of the origination city. Having the day or two buffer up front also allows your luggage extra time to catch up if necessary. I've been on cruises where people did not get their luggage until 5 or 6 days into the cruise. If you plan to fly in the day of the cruise, pack a couple of changes in your carry on bags.
The earlier you book your cruise, the more choices you have for planning excursions and/or private tours.
We like to go two nights before the cruise for the very reason you stated; the first day we're wiped from traveling plus the time difference, so the second day we use for sightseeing.
As for luggage, your chances for lost luggage are less if you use the same airline for the entire trip over. It's when you change airline that it can often create a problem. We also always suggest packing half of your clothes in each of the two suitcases just in case one makes and the other doesn't.
I also agree that May is the perfect time to do a Med cruise - much better than July. September can also be a very good time and often has some great deals.